Y12 Organic Chemistry Test

Name: ___________________________________________

Materials
For this paper you must have:
 A Periodic Table.
 A calculator, which you are expected to use where appropriate.

Instructions
 Answer all questions.
 You must answer the questions in the spaces provided.
 All working must be shown.
 Do all rough work in this book. Cross through any work you do not want
to be marked.
 Ensure your answers are clear and legible.

Information
The maximum mark for this paper is 40.
Time allowed: 45 mins.

Q1. This question is about the reactions of alkanes.

Page 1 of 14
(a) Alkanes can be used as fuels.

Give an equation for the combustion of heptane (C7H16) in an excess of oxygen.

___________________________________________________________________
(1)

(b) Heptane can be obtained from the catalytic cracking of hexadecane (C16H34) at a
high temperature.

Identify a suitable catalyst for this process.

Give one condition other than high temperature.
Give an equation for the catalytic cracking of one molecule of hexadecane to
produce one molecule of heptane, one molecule of cyclohexane and one other
product.

Catalyst ____________________________________________________________

Condition ___________________________________________________________

Equation ___________________________________________________________

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(3)

(c) Alkanes can be used in free-radical substitution reactions to produce

halogenoalkanes.

Give equations for the propagation steps in the reaction of butane to form 2-
chlorobutane.

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___________________________________________________________________
(2)

(d) Chlorofluorocarbons (CFCs) are a group of halogenoalkanes currently banned in

many countries. They cannot be used as solvents or refrigerants because of their
effect on the environment.

Page 2 of 14
 The structure of a CFC is shown.

Identify the radical produced from this CFC that is responsible for the depletion of
ozone in the atmosphere.

Explain, with the aid of equations, why a single radical can cause the decomposition
of many molecules of ozone.

Radical __________________________________________________________

Explanation ________________________________________________________

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(4)
(Total 10 marks)

Q2. The diagram shows some compounds made from a halogenoalkane.

Page 3 of 14
 (a) Draw the displayed formula of compound J.

(1)

(b) Name the mechanism for Reaction 2 and give an essential condition used to ensure
that CH3CH2CH2NH2 is the major product.

Name of mechanism __________________________________________________

Condition ___________________________________________________________
(2)

(c) Identify the reagent and conditions used in Reaction 3.

___________________________________________________________________
(1)

(d) Name and outline a mechanism for Reaction 3.

Name of mechanism __________________________________________________

Mechanism

(4)
(Total 8 marks)

Q3. This question is about 2-methylbut-1-ene.

Page 4 of 14
(a) Name the mechanism for the reaction of 2-methylbut-1-ene with concentrated
sulfuric acid.

Outline the mechanism for this reaction to form the major product.

Name of mechanism _________________________________________________

Outline of mechanism to form major product

(5)

(b) Draw the structure of the minor product formed in the reaction in part (a)

Explain why this is the minor product.

Structure of minor product

Explanation ________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(c) Draw the skeletal formula of a functional group isomer of 2-methylbut-1-ene.

(1)

(d) 2-methylbut-1-ene can form a polymer.

Page 5 of 14
 State the type of polymerisation.

Draw the repeating unit for the polymer formed.

Type of polymerisation _______________________________________________

Repeating unit

(2)
(Total 11 marks)

Q4. This question is about ethanedioic acid (H2C2O4) which is a dicarboxylic acid.

(a) Draw the skeletal formula of ethanedioic acid.

(1)

(b) Ethanedioic acid is formed by the oxidation of ethane-1,2-diol (HOCH2CH2OH).

State suitable reagent(s) and a condition for this reaction.

Reagent(s) _______________________________________________________

_________________________________________________________________

Condition _________________________________________________________

_________________________________________________________________
(2)

(c) Describe the colour change which would be observed.

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(1)

(Total 4 marks)

Page 6 of 14
Q5. Which compound has the greatest Mr?

(Total 1 mark)

Q6. What is the IUPAC name for this compound?

A 2-dimethyl-3-fluoropentane

B 2,2-dimethyl-3-fluoropentane

C 3-fluoro-2,2-dimethylpentane

D 3-fluoro-2-dimethylpentane

(Total 1 mark)

Page 7 of 14
Q7. Which of the arrows, labelled A, B, C or D in the mechanism in the diagram, is not correct?

D
(Total 1 mark)

Q8. Which statement about ethene is correct?

A It has no geometric isomers because there is free rotation

around the C=C bond.

B It reacts with HBr in a nucleophilic addition reaction.

C It burns in excess oxygen to produce carbon dioxide and water.

D The C=C bond is twice as strong as the C–C bond in ethane.

(Total 1 mark)

Q9. Three reagents are added separately to four organic compounds.

Which row shows the correct observations?

Sodium Acidified
Tollens’
hydrogen potassium
reagent
carbonate dichromate(VI)

orange solution no visible

A Propan-1-ol effervescence
turns green change

orange solution
B Propanal no visible change silver mirror
turns green

C Propanone no visible change no visible change silver mirror

Propanoic
D effervescence no visible change silver mirror
acid
(Total 1 mark)

Page 8 of 14
Q10. Which alcohol forms a mixture of alkenes when dehydrated?

A propan-1-ol

B propan-2-ol

C pentan-1-ol

D pentan-2-ol

(Total 1 mark)

Q11. For this question refer to the reaction scheme below.

Which one of the following reagents would not bring about the reaction indicated?

A Step 1 : alcoholic KOH

B Step 2 : aqueous Br2

C Step 3 : aqueous NaOH

D Step 4 : concentrated H2SO4

(Total 1 mark)

END OF QUESTIONS

Page 9 of 14
Mark schemes

Q1.
(a) C7H16 + 11O2 → 7CO2 + 8H2O
Ignore state symbols, Allow multiples
M1

(b) Zeolite OR aluminosilicate

Allow porous pot / aluminium oxide / alumina / silica / silicon dioxide
M1

Slight/moderate pressure
Slightly above atmospheric – allow 1-5 atmospheres / 100-500kPa
M2

C16H34 → C7H16 + C6H12 + C3H6

M3

(c)
If incorrect radical or ambiguous radical lose M1 but can
award M2 for ecf in each equation.
M1

Allow equations in either order

Allow dot anywhere on the second carbon
Ignore extra initiation and termination steps
M2
(d) Cl●
Allow Cl or Chlorine in M1 and M4
M1

Cl● + O3 → ClO● + O2
Penalise absence of dot once in the equations
M2

ClO● + O3 → Cl● + 2O2

Allow dot anywhere on the radical
Apply the list principle in the equations and penalise
Allow initiation from Cl2 as a 3rd equation
Allow equations in either order.

M3

Cl● is regenerated owtte

Ignore Cl● acts as a catalyst

Cl● is regenerated / reformed in 2nd equation (and causes a chain reaction in the
decomposition of ozone)
M4
[10]

Page 10 of 14
Q2.
(a)

Must be displayed
1

(b) Nucleophilic substitution

1

Excess NH3
Ignore aqueous, alcoholic, conc, dil, temp, heat, pressure
1

(c) NaOH/ ethanol or KOH / ethanol (both required)

NOT aqueous
Ignore heat, temp, conc., dil,
Accept alcoholic for ethanol
1

(d) (Basic) Elimination

Also credit E1 mechanism

If nucleophilic substitution shown then allow M3 only in mechanism

If wrong haloalkane used then Max 2 for mechanism

M3 curly arrow for loss of Br− & structure of carbocation
M1 arrow from lone pair on O of hydroxide to H (or to space
mid way between hydroxide O and H) (same as E2)
M2 arrow from C-H bond to C-C bond (same as E2)
3
[8]

Page 11 of 14
Q3.
(a) Electrophilic addition

NB Allow fully displayed or other structural formulae

if H2O used as electrophile − max 4 ONLY

M2 must show an arrow from = of C=C towards the H atom of the H−O
bond or HO that is part of H−O−S−… on a compound with molecular
formula H2SO4

M2 could have arrow to H+ in which case M3 would be for an

independent H−O bond break on a compound with formula H2SO4

M3: must use an arrow to show the breaking of the H−O bond
M3 ignore partial charges unless wrong

M4: is for the correct carbocation structure

NOT M4 if primary carbocation shown.

M5: must show an arrow from a lone pair of electrons on the correct
oxygen of the negatively charged ion towards the positively charged
carbon atom
M5 NOT HSO4
credit as shown or as: OSO3H − in which case negative
charge can be shown anywhere ECF from H2SO3 in M2

NB: The arrows are double-headed

IGNORE subsequent use of water to hydrolyse
hydrogensulfate
M1M2M3M4M5

(b)

If tertiary shown here allow as ECF for M1 if primary shown

in (a)
M1

(major) product formed via more stable carbocation OR tertiary

carbocation more stable (than primary)

Page 12 of 14
 Must be clear answer refers to intermediate and not product
M2

Due to electron-releasing character / (positive) inductive effect of three

alkyl groups (as opposed to one)
Primary has one e− donating alkyl group
M3

(c) Skeletal formula of cycloalkane

ignore structure of 2-methylbut-1-ene

1

(d) Addition (polymerisation)

Not additional
Penalise incorrect attachment of ethyl group
Must have trailing bonds
Ignore n and brackets
Ignore structure of 2-methylbut-1-ene
M1M2
[11]

Q4.
(a)

Any correct skeletal representation, but alcohol H’s should

be shown and C atoms should not be shown

Page 13 of 14
 (b) M1 acidified potassium dichromate(VI) or sulfuric acid & potassium
dichromate(VI)
M1 H2SO4 and K2Cr2O7 or H+ and K2Cr2O7
do not need (VI), but if oxidation state given it must be
correct
allow other strong acids
1

M2 reflux M2 need an attempt at an oxidising agent in M1

1

(c) Orange to green; Need full colour change to score mark.

1

[8]

Q5.
A

[1]

Q6.
C
[1]

Q7.
C
[1]

Q8.
C
[1]

Q9.
B
[1]

Q10.
D
[1]

Q11.
B
[1]

Page 14 of 14